191479-34-2Relevant academic research and scientific papers
Copper-catalyzed aerobic aliphatic C-H oxygenation with hydroperoxides
Too, Pei Chui,Tnay, Ya Lin,Chiba, Shunsuke
, p. 1217 - 1225 (2013/07/26)
We report herein Cu-catalyzed aerobic oxygenation of aliphatic C-H bonds with hydroperoxides, which proceeds by 1,5-H radical shift of putative oxygen-centered radicals (O-radicals) derived from hydroperoxides followed by trapping of the resulting carboncentered radicals with molecular oxygen.
Kinetic resolution of hydroperoxides with enantiopure phosphines: Preparation of enantioenriched tertiary hydroperoxides
Driver, Tom G.,Harris, Jason R.,Woerpel
, p. 3836 - 3837 (2008/02/13)
An efficient reductive kinetic resolution strategy capable of accessing optically active tertiary hydroperoxides is reported. Readily accessible tertiary hydroperoxides are resolved with commercially available (R)- or (S)-xylyl-PHANEPHOS with selectivity factors as large as 37. The resulting bis(phosphine oxide) can be recycled in high yields. The isolated mono(phosphine oxide) intermediate resolved hydroperoxides with the same selectivity as the parent bisphosphine. Copyright
Preparation of optically active tertiary alcohols by enzymatic methods. Application to the synthesis of drugs and natural products
Chen, Same-Ting,Fang, Jim-Min
, p. 4349 - 4357 (2007/10/03)
By the catalysis of AK or porcine pancreas lipases, 3-iodo-2-phenyl- 1,2-propanediol, 1-(hydroxy-methyl)-1-phenyloxirane, 2-(iodomethyl)-4- phenyl-3-butyne-1,2-diol, 2-(iodomethyl)-4-(trimethylsilyl)-3-butyne-1,2- diol, and 5,5-dimethyl-2-(iodomethyl)-3-hexyne-1,2-diol were resolved in very high enantioselectivities (E ≤ 153). The obtained enantiomerically pure or optically enriched compounds, containing an iodo atom, an oxirane moiety, or an alkynyl group, are versatile building blocks for the synthesis of chiral azido diols, sulfanyl diols, cyano diols, the side chain of a vitamin D3 metabolite, the ω-chain of a prostaglandin analog, and an aggregation pheromone (1S,5R)-(-)-frontalin. Models based on the consideration of the importance of size, distance, and electron effect are proposed to interpret the observed stereospecificity in the enzymatic reactions. Thus, the lipase- catalyzed reactions of 1,1-disubstituted 1,2-diols occurred efficiently at the primary hydroxyl groups while the enantioselectivity was controlled by the tertiary carbinyl centers.
